IPod won't update, says connection time out

I'm writing this for a friend i do a lot of computer help for.
His iPod Touch (first gen) will not update, consequentially he cannot update his new applications.
I would hate to restore it and wipe out everything but thus far, that's what I'm thinking we may have to do.
Any recommendations? It keeps saying that the connection timed out when downloading the 2.2 software.

You'll just have to make sure the playlists equal less tahn 20 (18.7) GB. This may mean cutting or two playlists down in size, or cutting one or two playlists.
Once you do that, go to edit\prefs\iPod, and check the boxes by all of the playlists totalling less than 20 GB.

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